Brominated vat dyestuffs of the benzanthronylaminoanthraquinone series



Patented May 12, 1936 UNITED STATES PATENT OFFICE BROMINATED VAT DYESTUFFS OF THE BENZANTHRONYLAIVIINOANTHRAQUIN- ONE SERIES Ernst Honold and Rudolf Miiller, Frankfort-on- I the-Main-Fechenheim, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application October 16, 1934, Serial No. 748,530. In Germany October 25, 1933 2 Claims. (01. 26036) Our invention relates to new brominated vat bluish green shades which in comparison with dyestufis and process of making same. the shades of the initial products are superior as If the vat dyestuffs of the general formula regards purity, bluish tint and fastness to ch10- rine.

5 X NH In order to further illustrate our invention the I II I following example is given the parts being by weight; but we wish it, however, to be understood that our invention is not limited to the particular products nor reacting conditions mentioned I therein: 10 X Example wherein one X means an acylamino-group and 25 Parts Of t y fi b a according to the other Xs mean hydrogen, which dyestufis U. S. Patent 1,850,562 by acting with benzoyl chloare described in U. s, Patents 1,350,562 a d ride on the alkaline condensation product of 1- 1,877,947, are treated according to the usual (bz1-benzanthrony1 amino) 5 aminoanthramethods with a halogen or a halogenating agent, quinene a e finely divided and a Solution of 16 in varying yields, often together with consider- Par Of bromine in about 200 Parts Of glacial able quantities of decomposition products, mixacetic acid, 25 parts of sodium acetate and a small 20 tures of dito tetrahalogenated. derivatives are q y of iodine a ad thereto- The obtained, which, it is true, are useful as interture is boiled for some hours under reflux while 20 mediates for further conversion reactions, but Stirring- The y s u formed Ce 11 to themselves only dye the fiber dull shades of no 12% of bromine and dyes cotton from a bluish practical interest. violet vat fast bluish olive shades of an improved Our present invention relates to low bromifastness to chlorine. The dyestufi dissolves in nated derivatives of the said starting materials concentrated sulfuric acid with a green color. 25 which are in eontradistinction to the above men- It corresponds to the formula tioned products of great tinctorial value owing to the fact that they are entirely free from decomposition products. These products are obtained by treating the said initial products with a brominating agent under such mild conditions as are not customary for the halogenation of vat dyestuffs. The reaction may be carried out with or without the addition of a diluent and a suitable catalyst.

The products obtained according to the above described processes correspond with the general formula wherein n is approximately the number 2.

The bromination may be carried out likewise for instance by acting with bromine in the presence of tetrachloroethane or nitrobenzene with or without the addition of iodine acting as wherein one X means an acylamino-group and catalyst. the other Xs mean hydrogen, n is approximately In the same manner the products obtained by 50 the number 2. The new dyestuffs dye the fiber the action of for instance benzoylchloride or 50 acetic acid anhydride on the alkaline condensation products of 1-(bz-l-benzanthronylamino) -4- mula X 0 NH- 7 V Br,l X 0 X wherein one X means an acetylaminoor ben- V 'zoylamine group and the other Xs mean hydrogen, n is approximately the number 2, which dyestuffs dye the fiber bluish green shades of great purity and. fastness to chlorine.

2. The brominated vat dyestufi of the formula 6 /\U 5 NH to 10 wherein n is approximately the number 2, which dyestuff dissolves in concentrated sulfuric acid with a green color and dyes cotton from a bluish violet vat bluish olive shades of a good fastness, particularly to chlorine. 2

ERNST HONOLD. RUDOLF MiiLLER. 

